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Asymmetric Strecker Synthesis of alpha-Arylglycines


Reference:

Perez-Fuertes, Y., Taylor, J. E., Tickell, D. A., Mahon, M. F., Bull, S. D. and James, T. D., 2011. Asymmetric Strecker Synthesis of alpha-Arylglycines. Journal of Organic Chemistry, 76 (15), pp. 6038-6047.

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Official URL:

http://dx.doi.org/10.1021/jo200528s

Abstract

A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure alpha-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords highly crystalline (S,S)-alpha-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-alpha-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-alpha-arylglycines. The enantiopurities of these (S)-a-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by (1)H NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

Details

Item Type Articles
CreatorsPerez-Fuertes, Y., Taylor, J. E., Tickell, D. A., Mahon, M. F., Bull, S. D. and James, T. D.
DOI10.1021/jo200528s
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code25269

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